


Windows and Virgins

by destinysbastard



Category: Supernatural
Genre: !!!, Abused Dean, Anal Sex, Blowjobs, Bottom!Cas, Dean Winchester's First Time, Dean needs to be held, Dubious Consent, First Time, Fluff, Gay Sex, M/M, Sex, Smut, Teasing, bottom!Dean, hurt!Dean, plus someone else's, top!Crowley, top!dean, virgins
Language: English
Status: Completed
Published: 2016-09-27
Updated: 2016-09-28
Packaged: 2018-08-18 03:52:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,195
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8148271
Author URL: https://archiveofourown.org/users/destinysbastard/pseuds/destinysbastard
Summary: The one in which Dean works as a window washer and two things happen twice:Dean gets some during his job, and a virgin is deflowered.





	1. Chapter 1

**Author's Note:**

> Chose not to use archive warnings, but read tags for further info. (Dub-Con!)
> 
> I'm sick which sucks (especially 'cause I have performances (singing) this week), but at least I got to finish this. :P
> 
> I am always happy for feedback, as well as corrections since I have no betareader.
> 
> Enjoy!

Dean had never pictured himself doing big things. But it didn't matter to him, as long as his brother was happy. And while Dean was not a school-person, Sammy's happiness looked something like Stanford. He was still finishing high school, but he kept telling Dean about all those colleges he'd like to apply to (Stanford was always at the top of his list), and Dean always thought about how he could help Sam's dream come true. So he worked all kinds of jobs, the best he could do after his unsuccessful (and unwanted) school career. Who would have thought the one he'd stick to (and the one where he'd learn the most) would be window-washing? Certainly not Dean.

***

22, green, bold eyes, freckles all over his face and a cocky smile, not to mention that lean body - that boy was a view. A view even prettier than his usual view across New York, with the sun setting over it, Crowley thought.

He had come in around 9:30am after a meeting and walked into his office, glad to be alone again. He'd poured himself a glass of 73' scotch and sat down in his office chair with a sigh. There were too many emails waiting to be answered. Today it bothered him more than usually, but he started working.

After an hour or so he had answered most of them and he stretched his arms out, only to notice how tense he was. So he got up, and after pouring himself another glass, he sat into his chair and turned around to look outside. And that's when he saw the young boy, cleaning his window. Enjoying the view and sipping his scotch, he thought to himself,  _Oh, I'll relax alright._

***

He liked the work. He moved a lot, didn't have to think much (but had time to sort his thoughts out) and now that he had done a few jobs already and didn't need instructions anymore, his coworkers left him pretty much alone, which he liked. He preferred being alone. But that day he wasn't.

He had just finished the window of a printer room and then he moved on to the next one. It took him a moment to realize there was someone sitting there, watching him. It was a middle-age, rather short man, with a scruffy beard and a self-satisfied smirk on his lips. Dean cleaned his windows, trying to ignore him as much as he could. But he felt those eyes piercing through him and it made him feel uncomfortable. Dean found him attractive, he couldn't help but steal a few glances now and then, but the way the man looked at him felt strange nevertheless, as if he was invading his privacy.

He was pulled out of his thoughts, when a window next to him opened and the man was standing there, smiling at him. Dean realized he'd been cleaning the same window over and over again, consumed in his thoughts, and blushed. Had he noticed?

But that's not why the guy had opened the window. "You look like you could use a break," he said. He offered him a glass of Scotch. "I shouldn't drink while I'm at work," Dean said. "I've got water too," the older man said.

Dean decided it would probably be better to do what the client said, since he wanted to keep his job, and so he put down his squeegee, walked across the carriage and went inside through the window.

The man welcomed him in with a smile and danger blinking in his eyes and Dean tried to swallow the upsetting feeling that had come up at that.  _"_ I'm Crowley," the man introduced himself. "Dean." They shook hands, and the way Crowley looked at him made his knees go weak. 

"I- I think I'll have that scotch anyway," Dean said and Crowley smiled. "Don't worry, I won't tell." Dean nodded and took the glass, downing it in one shot. Crowley frowned at him. "That scotch is probably older than you, treat it with more respect. You don't ex scotch." Dean apologized and Crowley poured him another glass, and it took Dean a lot of effort to drink it in small sips.

"That's the difference between scotch and men... Scotch tastes better the older it gets." Dean didn't know what to say at that. So that meant Crowley swung that way indeed... Was he flirting? Dean laughed a nervous laugh and Crowley looked amused.

"So how long have you been doing this for, Dean?" When Crowley said Dean's name in his accent, it sounded soft, like a purr. "Uh, just for a few weeks," Dean replied. "You like it?" Dean nodded. "Yeah... I can move a lot and stuff." Crowley took a few steps closer, and walked around him, eyeing his body. "You like moving? That's what I thought, with a body like that..."

He was now standing in front of Dean, who looked slightly red, and then he took Dean's empty glass and put it on his desk. He had an unreadable expression on his face and when he looked down at Dean's lips, Dean swallowed hard. There seemed to be a moment when both men were holding their breaths, standing so close, both knowing what would come next. When Crowley moved in close and kissed him, Dean was still surprised for a moment, but then he gave in to the kiss. After the tense and slow start, it turned dirty and rough real fast. Crowley pushed his tongue into Dean's mouth, and Dean tried to follow as much as he could. He was slightly overwhelmed with the older man's hands already on him, his body weight pressing him against the desk, and the sensation of that stubble against his face as he kissed him. This was nothing compared to those kisses he'd had as a teenager, sloppy and horny, but innocent in comparison to this.

Quickly and knowingly, without ever breaking the kiss or slowing down, Crowley's hands made their way from Dean's butt to his belt, soon opening it and freeing Dean's hard cock from his jeans that had become uncomfortably tight. Only then did the kissing stop - or at least move away from Dean's lips.

With a few touches, Crowley had Dean breathing and panting and ringing for air. Oh, how untouched that boy was.

Dean opened his eyes when Crowley's hands suddenly disappeared, and saw him open his belt and unzip his pants, revealing a huge dick. Dean had never seen anything like it in real life. He had watched porn, and had had one experience with a guy in high school, but this, this was something else.

"Do you like doing things with your mouth, too, Dean?" he asked and looked at Dean, his eyes heavy with lust. "I- I've never done this before," Dean said shyly, feeling himself blush. "Oh, don't worry, I'll tell you what to do," he said with a smirk.

So Dean got on his knees and wrapped his mouth around Crowley's cock, resulting in a low moan from the man above him. He licked, and tried to take in more, but it was way too big and he gagged for a moment, making it hard to breathe. It passed quickly though, and he was glad to have Crowley's instructions. "Use your hands where you can't reach with your mouth," he said, his breathing ragged as Dean did what he was told.

He moved his hand up and down Crowley's shaft, and squeezed his balls when Crowley told him to. He almost forgot to use his tongue, as he focused on the hands part - this kind of coordination wasn't easy.

His blowjob was sloppy and inexperienced but Crowley loved the view and got off on giving him orders. "Stop," he then said in a firm voice. Dean stopped and looked up. Had he done something wrong? But Crowley had more in mind than that sloppy blowjob.

He smirked. "Get up." Dean got up and when Crowley pulled a bottle of lube out of his drawer, he just stared. This was going just a little too fast. Not that he didn't want the whole sex thing, he did. He had wanted it for a long time, wondered and fantasized about it many a night. But this was a lot to take at once (literally), and he didn't even know the guy.

He tried to shake off those thoughts.  _You're getting what you've wanted for so long,_ Dean thought to himself. It would be stupid to back out now. He was no coward. 

"Don't worry, love," Crowley said, obviously noticing Dean's doubts. His ' _love'_ had been completely absent of real affection; such a loving word now sounded downright dirty and wicked. 

"I'll take care of you," he purred into Dean's ear, his hand again playing with Dean's dick, bringing it right back to life. It took Crowley no effort to turn Dean around and suddenly he had him bent over his desk. Dean was taken aback, but couldn't speak, his mind dazed with lust, suffocating the upsetting feeling that was settling in his stomach. All his thoughts melted away, when Crowley pushed a finger inside, working him lose and wide.

He soon added a second finger, then a third, every single one of Dean's moans going straight to his dick. Dean was so tight, his ass all pale and soft and untouched; and Crowley could not wait to break that barrier for the first time.

He had taken time, but was not patient enough to wait anymore. Dean could have used more preparation but Crowley knew he'd be fine, and he loved the tight feeling around him as he pushed into Dean with a grunt.

Dean only noticed he was holding his breath when Crowley told him to relax.

He breathed in, then out, biting onto his lip, and tried to relax, tried to will away the stinging pain that seemed to get worse with every second. But then it went away, or maybe he just stopped caring, when Crowley started relentlessly thrusting into him, hitting his prostate over and over again.

He was breathing hard, and soon white stars exploded in front of him, shivers ran through his whole body, and a moan escaped his mouth. He came all over the table and his own stomach. Crowley kept thrusting into him for another few moments, the vulgar sound of skin slapping against skin filling Dean's ears, and then he felt Crowley coming into him with a grunt. After a second he pulled out and zipped up his pants, quickly disappearing into the bathroom in his office.

Dean was still holding onto the desk when Crowley threw a washcloth in his direction. With the words "Clean up," he left to take a shower. Dean needed a moment to collect himself, then cleaned up the table and his own stomach as well as he could. When he pulled up his pants he felt Crowley all over him still. He looked in the direction of the bathroom, for a moment wondering if he should wait, and then he left.

He had not expected to feel this way at all. It took him a while until everything he  _had_ expected set in: that relief about losing his virginity, finding this new kind of confidence, and having sex quite regularly and liberally.

Maybe it had just been a bit much, his first time; after all it had not been innocent and some teenage fling, but  _real_ sex with someone who had experience. He forgot about it soon and enjoyed his new-found liberty.

 


	2. Chapter 2

Window after window he cleaned with long, absent-minded, familiar brushes that he had done a million times now. He was good at his job, and he liked it a lot.

It wasn't the best-paid job ever, but it had been enough (especially with his many work-hours) to get Sammy into university.

Grey skies hung heavily over Dean, and he hoped it wouldn't rain. This window was one of the last though and he'd be done earlier than planned, so no need to worry.

He had gotten used to sometimes being watched through the window, or exchanging awkward glances. He was more confident than he'd been a few years ago and he didn't really mind anymore; he'd just quickly finish his work and move on.

When those blue eyes stung into him, it was different though. It came unexpected and it was definitely not as easily brushed off as all those other glances before.

He had just started to clean another window, and when that young man on the other side of the window looked up at him, his hand froze.

The brown-haired guy looked away rather quickly and maybe Dean imagined it, but he thought he saw a light blush spread over his cheeks.

Considering how shy he seemed, his gaze had been anything but timid.

Dean tried to focus on his work, even though he could feel the younger man looking at him still. It worked fine - until it suddenly started raining.

Thick raindrops started hitting the carriage and Dean started swearing to himself, annoyed that he had gotten distracted. He was sure, if he had kept working with that pace he had had before meeting the gaze of that blue-eyed beauty, he would have finished before the rain.

But here he was. Damned as always.

"Do you wanna come in?" he heard a low voice next to him. He turned around and met those blue eyes again.

"Yeah, thanks," he muttered, before climbing into the office through the window.

The other man shut the window quickly and then turned around to face Dean.

"That came out of nowhere, huh?" he said, a little bit awkwardly.

"Yeah..." Dean just replied. Not really out of nowhere, but he wouldn't throw off that poor guy who was just trying to make small talk.

"I'm Cas, by the way." Cas held out his hand and Dean took it. Cas' hand shake was firm and his hands were soft. In comparison Dean's were probably all rough and dry, the hands of a window washer.

"Dean," he introduced himself. Cas smiled.

For a moment they just stood there, looking at each other (with rather goofy looks on their faces).

"Do you uh- wanna sit?" Cas asked and Dean glanced outside. "Doesn't look like it's gonna stop anytime soon."

Cas motioned for a chair and Dean sat down across from him. Again, they just looked at each other, both not finding any strength for small talk, and also too fascinated about each other.

Then Dean realized it was Cas' office - he'd probably have to work.

"I don't want to keep you from anything though," he quickly said.

"Oh... You're not. I've got time." What did that mean? Was he fed up with his work? Dean would understand, he'd never been one for office jobs. But what did he mean by 'I've got time'? Time for what?

Dean smiled, and he felt very stupid suddenly.

What was he doing, being all awkward and shit? That wasn't him.

If he found someone attractive, he'd show it. But from the first moment he had seen Cas, there had been something different about him. Something that fascinated Dean in a more profound way.

But yes, of course he was attracted to him.

"What do you do anyway?" Dean asked. "Accounting. Not very exciting. But, uh, it gets you money, so..." Dean nodded. He got the money thing, but he still wouldn't do a job he couldn't stand simply for the money. For Sammy yes. But even window washing did the job.

"I lost my parents when I was very young, so I kind of needed that to get out of the whole system and be independent."

"Oh. I'm sorry," Dean said. It was more of an automatic response. That's what you're supposed to say when someone tells you something like that, isn't it?

Mostly he was just confused about his feelings. Why was Cas telling him this? Why was he opening up to him? Dean was not used to that, especially from potential hookups.

"Do you want something to drink?" Cas asked, getting up. "Water?"

"Yeah, sure," Dean replied and got up as well. Cas filled him a cup with water from the water dispenser. "Thanks." He took the cup and drank a bit, then put it onto the desk. Then he took a few steps around the office and looked at the books in the big wooden bookshelves next to the desk.

Cas followed him. "Got a lot of books, huh?" Dean said, looking up at the tall bookshelf. They were standing close.

Cas smiled. "Yeah. I don't know, I always loved reading. There is something so relaxing to it. And I just love..." His voice trailed off when he looked at Dean who had come closer and was shamelessly staring at him. First those blue eyes, and then those lips...

When Cas stopped talking, Dean looked up at him. Cas was slightly blushing - this time Dean definitely did  _not_ imagine it -, and also gazing back at Dean's lips.

Dean moved in, his right hand settling on Cas' waist, his left hand on his cheek, softly holding him. Cas' lips were even softer than Dean had imagined them to be, and they tasted sweet.

Dean's tongue was quickly involved, and Cas started licking and exploring Dean's mouth, a little bit more shyly, too.

Leaning against the bookshelf, they moved closer together, Dean's hands slowly carressing Cas' back and sides. They sometimes came up for air, and only then were they aware of how their breathing had sped up.

Dean somehow walked Cas over to the desk, without ever breaking their embrace.

At first Cas just leaned against it, then he sat up onto the table, Dean standing in between his legs.

Cas' hands were behind Dean's neck, now starting to move, mostly to play with his hair. Dean loved the feeling of that. He wasn't sure if anyone had ever played with his hair like that, even more so while making out.

His lips moved from Cas' mouth to his neck, where his licks and soft bites produced quiet but wonderful sounds from Cas. He smiled into his skin, when Cas huffed, "Oh  _god_ " at Dean's hands making their way to Cas' pants.

They were yet just hovering over his obviously excited dick, massaging it through the fabric. Each of Cas' breaths and moans went right to Dean's cock, which was already strained against his jeans.

Eventually he opened Cas' belt and then unzipped his pants, his fingers slipping into the waistband of his boxers.

Cas looked up at Dean, his blue eyes a darker shade now. Dean just smirked, before going down on him.

Cas sucked in air, and then exhaled, his whole body tensing up at the sensations of Dean's lips around his cock. Dean licked, kissed, swallowed down on his whole length and felt very satisfied with the sounds he was provoking from Cas.

From the way Cas was squirming and writhing above him, he knew he was already close. But that's not how Dean wanted him.

So he released his dick, and planted a kiss on Cas' lips before opening his own pants.

In the midst of the heat, Cas' thoughts caught up with him for a moment. This felt amazing, but wasn't this all going to fast?

Dean moaned at finally freeing his dick, and then looked up at Cas. "Do you have any lube?" he asked. Cas was just staring, sitting there, completely out of breath.

"Are you okay?" Dean asked. Cas looked up at him and found his voice again. "Yeah... Yeah, I just... I've never done this before," he confessed and looked away.

Those words took Dean right back to his first time, 5 years ago. A lot of time had passed ever since, and Dean rarely thought about it, but now everything came back to him.

He'd been scared. He wouldn't have wanted to admit it, but he'd been scared. He didn't even really know of what - maybe disappointing the older man, not being enough, or that it would hurt, or that he'd regret it. Regret having it like this. He sometimes did.

He'd never want Cas to regret it.

"That's okay... But.. do you want to?" he asked, his voice suddenly softer.

Cas looked back up at him. After a moment he nodded, seeming more calm again. Dean smiled, then moved closer again and planted a soft, loving kiss on Cas' lips. They both cherished this moment, just breathing into each other.

Dean's hand was resting on Cas' thigh and now moved over again, fastening Cas' breath again with a few lustful strokes, their faces still close.

Cas' words took him a little by surprise. "Second drawer," he breathed.

With one hand still on Cas, Dean opened the drawer and found the lube. Dean put it on the desk.

He took Cas into his arms and lifted him off the desk, planting kisses on his shoulders and neck again, his hands carressing his butt. Then he turned him around and, still bent over him, his chest against Cas' back, his lips right next to Cas' ear, he whispered, "Don't worry, I'll take care of you."

And he meant it.

He put lube on his fingers and started massaging Cas' hole very softly. He soon pushed one finger in carefully, resulting in lovely little sighs from Cas.

He was warm and soft and tight, and Dean took his time.

He added a second finger in, and for a moment Cas tensed up, but then managed to relax against Dean's fingers.

On the third, Cas tensed up more and Dean went slower and kissed the back of his neck, his free hand resting on Cas' hand on the desk, until Cas relaxed again.

When Dean took out his fingers, Cas mourned the loss. But Dean would fill him up with something more soon enough.

Rolling on a condom and getting some lube on his cock too, Dean got ready and then aligned his length with Cas' hole.

"You okay?" Dean asked. He needed to be sure. "Yes," Cas replied.

His neck and cheeks were flushed red and he was already breathing hard.

Dean smiled to himself.

He softly grabbed Cas' buttcheeks and pushed them apart, making the entrance easier. Then he slowly,  _slowly_ pushed in. 

Cas hissed and moaned and held his breath, and before going in further, Dean bent forward and whispered, " _Relax_ ." Cas nodded and tried to breathe deeper again.

Dean was hesitating. He didn't want to, but he kept remembering how he was bent over a desk, trying to breathe away the pain. He knew now, it does hurt, but it isn't supposed to hurt like  _that_ . Was he hurting Cas? How should he know? He had not said anything either.

Again, he asked if he was okay, realizing he never asked like that. Cas said  _yes_ again, this time more convincing. 

" _Need you, Dean,_ " he begged, "Need you to fill me."

Dean loved to hear him beg, and was even happier to meet his wishes, finally pushing in further.

He started thrusting, not too hard, but enough to make them both pant and moan.

" _Cas,_ " Dean sighed, pushing in further, now hitting his prostate every few thrusts.

Cas only replied with moans, each louder than the previous.

Quite soon, clenching tightly around Dean's cock, grunting his name, and his hands pushing back against the desk, he came, and very soon after Dean did too.

The only sound filling the room was both of their breathing, shallow and quick, but now slowing down.

Dean slowly pulled out, making Cas wince, and all he wanted to do was collapse onto the desk, with Cas in his arms.

He pulled off the condom and threw it into the bin under the desk, then got some toilet paper and, after taking Cas' hand and turning him around, he wiped off Cas' stomach and the desk as well as he could. He zipped up his pants and so did Cas.

He saw himself standing there, dirty, unravelled and vulnerable; simply left to himself. He remembered the empty, and yet heavy feeling in his stomach, as if it had been only a week ago.

He wanted to make sure Cas didn't feel that way. Though he didn't know how exactly he was supposed to do that. But he didn't have to do much, as Cas now put his arms around him and hugged him.

Dean was taken a bit by surprise, but then he hugged Cas back.

They just stood there like that, breathing each other in, and it felt more intimate to Dean than sex had ever felt.

It came out of nowhere, when Dean started crying, only a few silent tears running down his cheeks. His breathing got hitched and his torso tensed up, and he was just as surprised as Cas, if not more so.

Cas tightened his embrace and pulled him in closer.

Dean had not expected to be the one who needed to be held most.

 

 

**Notes for the Chapter:**

> I had quite a bit of fun with this, it was interesting to explore how Dean became Dean (in the sense of his sexual behaviour) and how he would finally admit to himself that he wasn't okay with what happened, and my heart is all about how Cas and Dean take care of each other. I love it. 
> 
> I hope you enjoyed reading this as much as I enjoyed writing it, and seeee yaaaaa soon :D


End file.
